Sodium Azide → Diethyl 3-azidopropylphosphonate

HRID 1713033Notes

Reaction equation

HRID 1713033 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11]Br)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[N-:13]=[N+:14]=[N-:15].[Na+]>CC(C)=O>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][N:13]=[N+:14]=[N-:15])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 283500Diethyl (3-bromopropyl)phosphonate

Product 1

HCID 10867835Diethyl 3-azidopropylphosphonateYield 98.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(3-Bromopropyl)phosphonic acid diethyl ester (300 mg, 1.15 mmol) and sodium azide (150 mg, 2.3 mmol) were dissolved in acetone (10 ml) and the solution was refluxed for 12 hours under nitrogen atmosphere, then cooled to room temperature, filtered, and dried under vacuum to afford (3-azidopropyl)phosphonic acid diethyl ester (250 mg, 98% yield) as a colorless liquid.

Workup

  1. temperaturethe solution was refluxed for 12 hours under nitrogen atmosphere
  2. filtrationfiltered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-976575b76c224660bcc9453766298d3d
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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